50 days in Vermont Itinerary

50 days in Vermont Itinerary

Created using Inspirock Vermont attractions planner
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Make it your trip
+2
Ferry to Billy Bishop Toronto City, Fly to Montreal, Bus to Burlington
1
Burlington
— 11 nights
Drive
2
Jay
— 9 nights
Drive
3
Saint Johnsbury
— 10 nights
Drive
4
Woodstock
— 10 nights
Drive
5
Bennington
— 9 nights
Drive

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Burlington — 11 nights

Burlington is the most populous city in the U.S. state of Vermont and the seat of Chittenden County. Attractions like Church Street Marketplace and North Beach Park make great kid-friendly stops. Explore the numerous day-trip ideas around Burlington: Stowe (The Alchemist, Stowe Recreation Path, &more), Lake Champlain Maritime Museum (in Vergennes) and Waterbury Center (Cabot Farmers' Store & GreenSpark Sustainability Park). There's lots more to do: trek along Burlington Bike Path, enjoy the sand and surf at Alburg Dunes State Park, relax in the rural setting at Morse Farm Maple Sugarworks, and walk around Waterfront Park.

To see more things to do, maps, ratings, and other tourist information, you can read our Burlington travel planning site.

Toronto, Canada to Burlington is an approximately 7.5-hour combination of ferry, flight, and bus. You can also drive; or do a combination of train and bus. In July, daytime highs in Burlington are 32°C, while nighttime lows are 19°C. Cap off your sightseeing on the 15th (Wed) early enough to go by car to Jay.
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Parks · Outdoors · Breweries & Distilleries · Nature
Side Trips

Jay — 9 nights

Jay is one of the northernmost towns in Orleans County, Vermont, United States, located on the Canada–US border. Kids will appreciate attractions like Jay Peak Pump House and Jay Peak Ski Resort. Change things up with these side-trips from Jay: Jed's Maple Products (in Derby), Grand Isle State Park (in Grand Isle) and Newport Bike Path (in Newport). There's still lots to do: fly down the slopes at Jay Peak Resort, take in the dramatic scenery at Big Falls, hike along Hazen's Notch, and contemplate the long history of Tea at the Governor's House.

For photos, more things to do, other places to visit, and more tourist information, refer to the Jay trip planner.

Traveling by car from Burlington to Jay takes 1.5 hours. Prepare for slightly colder weather when traveling from Burlington in July: high temperatures in Jay hover around 28°C and lows are around 15°C. You will leave for Saint Johnsbury on the 24th (Fri).
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Parks · Nature · Outdoors · Breweries & Distilleries
Side Trips

Saint Johnsbury — 10 nights

St. Attractions like Museum of Everyday Life and Bread and Puppet Theater make great kid-friendly stops. Change things up with these side-trips from Saint Johnsbury: Martin Bridge Park (in Marshfield), Barre (Hope Cemetery & Vermont Granite Museum) and Bragg Farm Sugar House & Gift Shop (in Montpelier). There's lots more to do: stroll around Dog Mountain Home of Stephen Huneck Gallery, admire the masterpieces at St. Johnsbury Athenaeum, admire the majestic nature at Elmore State Park, and admire all the interesting features of The Long Trail.

For traveler tips, more things to do, ratings, and more tourist information, refer to the Saint Johnsbury trip itinerary planner.

Drive from Jay to Saint Johnsbury in 1.5 hours. July in Saint Johnsbury sees daily highs of 30°C and lows of 17°C at night. Finish your sightseeing early on the 3rd (Mon) so you can drive to Woodstock.
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Parks · Nature · Museums · Outdoors
Side Trips

Woodstock — 10 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Attractions like Montshire Museum of Science and Quechee Gorge make great kid-friendly stops. Venture out of the city with trips to Killington (Killington Resort & Killington - Pico Adventure Center), Rutland (Rutland murals & Wonderfeet Kids Museum) and Pond Hill Ranch (in Castleton). Next up on the itinerary: experience rural life at Sugarbush Farm, explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park, snap pictures at Taftsville Covered Bridge, and take in the awesome beauty at Mount Tom.

To see reviews, other places to visit, and more tourist information, read Woodstock journey builder site.

Traveling by car from Saint Johnsbury to Woodstock takes 1.5 hours. In August in Woodstock, expect temperatures between 32°C during the day and 15°C at night. Finish your sightseeing early on the 13th (Thu) so you can drive to Bennington.
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Parks · Historic Sites · Outdoors · Nature
Side Trips

Bennington — 9 nights

Bennington is a town in Bennington County, Vermont, in the United States. Kids will appreciate attractions like Hildene, The Lincoln Family Home and Harriman Reservoir. Explore the numerous day-trip ideas around Bennington: Manchester (Equinox Preservation Trust, Dana L. Thompson Memorial Park, &more), Bromley Mountain (in Peru) and Vermont Country Store (in Weston). There's lots more to do: get great views at Bennington Battle Monument, stroll the grounds of New Catholic Cemetery, explore the world behind art at Bennington Museum, and snap pictures at Silk Road Covered Bridge.

To see other places to visit, traveler tips, and tourist information, use the Bennington vacation builder site.

Traveling by car from Woodstock to Bennington takes 2 hours. Alternatively, you can take a bus. In August in Bennington, expect temperatures between 30°C during the day and 15°C at night. Wrap up your sightseeing by early afternoon on the 22nd (Sat) to allow enough time to drive back home.
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Parks · Nature · Winter Sports · Outdoors
Side Trips

Vermont travel guide

4.5
Gift & Specialty Shops · Ski Areas · Historic Sites
The Green Mountain State
Known for its autumn foliage and maple syrup, Vermont is one of the country's smallest states in terms of both population and geographic area. Despite its small size and mostly rural character, the state boasts many picturesque places to visit, including Lake Champlain, one of the nation's largest freshwater bodies. Split in half by the Green Mountains--a popular holiday destination for hiking and skiing--Vermont features a rolling landscape dotted with farms and quaint towns known for their family-run inns, antique shops, and restaurants. Be sure to explore the state's many wild areas while on vacation, but beware of the so-called "mud season," a period of a few weeks when the state's unpaved roads become undrivable due to spring thaw.
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